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| 血管阻断剂活性化合物AVE-8063的合成 | |
| 引用本文： | 黄琦,黄桐堃,倪庆纯,魏文,徐田龙,张恩生,吕泽良,邹永.血管阻断剂活性化合物AVE-8063的合成[J].精细化工,2013,30(5):549-554. |
| 作者姓名： | 黄琦 黄桐堃 倪庆纯 魏文 徐田龙 张恩生 吕泽良 邹永 |
| 作者单位： | 1. 中国科学院广州化学研究所,广东广州510650;中国科学院大学,北京 100039 2. 中国科学院广州化学研究所,广东广州,510650 3. 广州医药研究总院,广东广州,510240 |
| 基金项目： | 国家自然科学基金(批准号：21272280)；广东省中国科学院全面战略合作项目(批准号：2009B091300125)；广东省战略新兴产业核心技术攻关项目(批准号：2011A081401002)；“十二五”国家重大新药创制项目(批准号：2011ZX09202-101-07)和广州市科技计划项目(批准号：12A51061555) |
| 摘 要： | 对血管阻断剂活性分子(Z)-3'-氨基-3,4,4',5-四甲氧基二苯乙烯(AVE-8063)的合成进行了研究。以对甲氧基苯乙酸(Ⅰ)为原料,经溴代及Perkin反应得到(E)-2-(3-溴-4-甲氧基苯基)-3-(3,4,5-三甲氧基苯基)丙烯酸(Ⅲ),再经芳环上溴的氨基取代得到(E)-2-(3-氨基-4-甲氧基苯基)-3-(3,4,5-三甲氧基苯基)丙烯酸(Ⅳ),最后在Cu/1,10-Phen/PEG-400体系微波辅助下反应6 min即脱羧得到目标化合物(Ⅴ),总收率为60.1%。产物结构经IR、MS和1HNMR确证。 |
| 关 键 词： | AVE-8063 二苯乙烯类化合物 脱羧 Perkin反应 血管阻断剂 医药与日化原料 |
| 收稿时间： | 2012/12/13 0:00:00 |
| 修稿时间： | 2013/1/15 0:00:00 |
A Simple and Efficient Method for The Synthesis of Vascular Disrupting Agent AVE-8063 |
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| HUANG Qi,HUANG Tong-kun,NI Qing-chun,WEN Wen,XU Tian-long,ZHANG En-sheng,LV Ze-liang and ZOU Yong.A Simple and Efficient Method for The Synthesis of Vascular Disrupting Agent AVE-8063[J].Fine Chemicals,2013,30(5):549-554. | |
| Authors: | HUANG Qi HUANG Tong-kun NI Qing-chun WEN Wen XU Tian-long ZHANG En-sheng LV Ze-liang and ZOU Yong |
| Affiliation: | Guangzhou Institute of Chemistry, Chinese Academy of Sciences,Guangzhou General Pharmaceutical Research Institute,Guangzhou Institute of Chemistry, Chinese Academy of Sciences,Guangzhou Institute of Chemistry, Chinese Academy of Sciences,Guangzhou Institute of Chemistry, Chinese Academy of Sciences,Guangzhou Institute of Chemistry, Chinese Academy of Sciences,Guangzhou Institute of Chemistry, Chinese Academy of Sciences |
| Abstract: | A new synthetic protocol leading to the vascular disrupting agent(Z)-3′-amino-3,4,4′,5-tetramethoxylstilbene(AVE-8063) was successfully devised.Starting from 4-methoxyphenylacetic acid,(E)-2-(3-bromo-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl) acrylic acid(Ⅲ) could readily be obtained through bromination and Perkin condensation.Amination of Ⅲ afforded(E)-2-(3-animo-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)acrylic acid(Ⅳ),which was subsequently decarboxylated in Cu/1,10-Phen/PEG-400 system under microwave conditions for 6 min to give the target product(Ⅴ) with a total yield of 60.1%.The structure of the product was verified by IR,MS and 1HNMR. |
| Keywords: | AVE-8063 stillbenes decarboxylation Perkin Reaction Vascular Disrupting Agents |
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